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Method for preparing 5-hydroxymethyl-2-furfural using acid catalyst in presence of ethylene glycol-based compound solvent derived from biomass

a technology of methyl-2 furfural and acid catalyst, which is applied in the direction of physical/chemical process catalyst, organic chemistry, chemistry apparatus and processes, etc., can solve the imbalance between market demand and supply, the chemical industry's dependence on petroleum, and the era of high oil prices. , to achieve the effect of reducing the dependence of petroleum, high yield and effective separation

Active Publication Date: 2017-10-31
KOREA INST OF IND TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present disclosure provides a method for preparing 5-hydroxymethyl-2-furfural using a biomass-derived non-petroleum solvent, which can reduce the chemical industry's dependence on petroleum and help regulate greenhouse gases. The method allows for high yield production of 5-hydroxymethyl-2-furfural from fructose, and the solvent and catalyst can be separated and reused after the reaction.

Problems solved by technology

Because of their finite reserves, global petroleum resources are running out.
With many developing countries currently industrializing, petroleum demand has sharply increased, causing an imbalance between market demand and supply and leading to an era of high oil prices.
Furthermore, the reckless use of petroleum has brought about an explosive increase in greenhouse gases, provoking significant environmental problems such as global warming.
As for TPA, its synthesis based on biomass has not yet been achieved.
Extensive studies have been directed toward the mass production of HMF, but none have yet succeeded in developing processes for the industrial mass production of HMF.
However, the direct extraction of HMF from the DMSO solvent is difficult not only because DMSO is difficult to remove by distillation due to its high boiling point of 189° C., but also because DMSO is miscible with most solvents.
However, only a limited amount of HMF can be extracted from the solvent system, and the solvent cannot be reused.
However, DMF still has a high boiling point (153° C.) and ionic liquid is economically unfavorable for use in industrial mass production due to its high price.

Method used

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  • Method for preparing 5-hydroxymethyl-2-furfural using acid catalyst in presence of ethylene glycol-based compound solvent derived from biomass
  • Method for preparing 5-hydroxymethyl-2-furfural using acid catalyst in presence of ethylene glycol-based compound solvent derived from biomass
  • Method for preparing 5-hydroxymethyl-2-furfural using acid catalyst in presence of ethylene glycol-based compound solvent derived from biomass

Examples

Experimental program
Comparison scheme
Effect test

example 1

[0096]In a 38 mL thick-glass-walled pressure tubular reactor (having an O.D. of 25.5 mm and a length of 20.3 cm) equipped with a Teflon screw cap, a fructose syrup (150 mmol, 25% water) was placed, together with the solid acid catalyst Amberlyst-15 (300 mg), followed by adding the EG-based solvent monoethylene glycol dimethyl ether (3 mL). The resulting solution was heated at 120° C. for 2 hrs while stirring at 700 rpm. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted 100-fold in distilled water. HPLC and 1H NMR analyses were conducted, and the data are depicted in FIGS. 1 and 2, respectively.

[0097]As can be seen in FIGS. 1 and 2, 1H NMR data identified the product as HMF while HPLC data indicated the production of HMF at a yield of 80%.

example 2

[0098]In a 38 mL thick-glass-walled pressure tubular reactor (having an O.D. of 25.5 mm and a length of 20.3 cm) equipped with a Teflon screw cap, a fructose syrup (150 mmol, 25% water) was placed, together with the solid acid catalyst Amberlyst-15 (300 mg), followed by adding the EG-based solvent 1,4-dioxane (3 mL). The resulting solution was heated at 120° C. for 2 hrs while stirring at 700 rpm. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted 100-fold in distilled water. HPLC analysis was conducted, indicating the production of HMF at a yield of 78%.

example 3

[0099]In a 38 mL thick-glass-walled pressure tubular reactor (having an O.D. of 25.5 mm and a length of 20.3 cm) equipped with a Teflon screw cap, a fructose syrup (150 mmol, 25% water) was placed, together with the solid acid catalyst Amberlyst-15 (300 mg), followed by adding the EG-based solvent diethylene glycol dimethyl ether (3 mL). The resulting solution was heated at 120° C. for 2 hrs while stirring at 700 rpm. After completion of the reaction, the reaction mixture was cooled to room temperature and diluted 100-fold in distilled water. HPLC analysis was conducted, indicating the production of HMF at a yield of 79%.

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Abstract

Provided is a method for preparing 5-hydroxymethyl-2-furfural using an acid catalyst in the presence of an ethylene glycol-based solvent. The method for preparing the 5-hydroxymethyl-2-furfural involves using a linear or cyclic ethylene glycol-based compound as a solvent and producing the 5-hydroxymethyl-2-furfural from fructose, in the presence of the acid catalyst, thereby reducing the dependency on petroleum in response to greenhouse gas emission regulations. Also, a high yield of the 5-hydroxymethyl-2-furfural can be obtained from fructose, and the solvent and the catalyst can be efficiently separated, collected, and reused after a reaction has completed.

Description

[0001]This is a U.S. national stage application of PCT Application No. PCT / KR2014 / 008034 under 35 U.S.C. 371, filed Aug. 28, 2014 in Korean, claiming the priority benefit of Korean Application No. 10-2013-0103028, filed Aug. 29, 2013, which is hereby incorporated by reference.TECHNICAL FIELD[0002]The present disclosure relates to the preparation of 5-hydroxymethyl-2-furfural. More particularly, the present disclosure relates to a method for preparing 5-hydroxymethyl-2-furfural, a platform compound for high value-added biofuels or biochemicals, from fructose using a biomass-derived ethylene glycol-based solvent and an acid catalyst.BACKGROUND ART[0003]Because of their finite reserves, global petroleum resources are running out. With many developing countries currently industrializing, petroleum demand has sharply increased, causing an imbalance between market demand and supply and leading to an era of high oil prices. Furthermore, the reckless use of petroleum has brought about an ex...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07D307/50C07D307/46
CPCC07D307/46B01J27/053C07D307/48
Inventor CHO, JIN KUKIM, SANG YONGKIM, BO RASHIN, SEUNG HAN
Owner KOREA INST OF IND TECH